Novel chemical agents comprising an adenosine moiety or an adenosine analog moiety and an imaging moiety and methods of their use
a technology of chemical agents and adenosine analogs, applied in the field of new chemical agents, can solve the problem that no adenosine-based agents have been developed for myocardial imaging
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example 1
[18F]-5′Fluoroadenosine
2′,3′ isoproylidene adenosine
[0118] A 250 ml round bottom flask was charged with 10 gm adenosine and to it was added 100 ml acetone. Methanesulfonyl chloride (10 ml) was then added drop-wise to the above solution. The solution was stirred for 30 minutes, after which time 100 ml of 1M Na2CO3 was carefully added. This sample was stirred for another 30 minutes and the solution filtered. The filtrate was taken up in dichloromethane, washed with water, and dried. The organic solvent was removed to afford the 4.45 grams pure 2′,3′ isopropylidene adenosine as the product.
5′-Tosyloxy 2′,3′-isopropylidene adenosine
[0119] To a 100 ml flask was added 250 mg of the isopropylidene adenosine. To this sample was added THF (3 ml) followed by NaH (29.2 mg). This was stirred for 20 minutes at room temperature after which p-toluenesulfonyl chloride was added in one lot (232 mg). The mixture was stirred for 20 minutes after which it was deemed complete by LC-MS (Liquid Chroma...
example 2
2-Aminoadensosine
2-aminoadenosine
[0124] To 1.0 gm of dry guanosine (7.06 mmol) was added dry pyridine and this was cooled to 0° C. in a ice bath. This was followed by drop-wise addition of trifluoroacetic anhydride (4.9 ml, 35.3 mmol). The above solution was stirred for 30 minutes after which an additional 2.5 ml trifluoroacetic anhydride was added and the solution was stirred for an additional 30 minutes. 20 ml of cold, concentrated aqueous ammonia was then added to the above solution and stirring was continued for an additional 1.5 hrs, after which the mixture was evaporated to dryness and the residue dissolved in water and purified using reversed phase HPLC (Luna C18;; Flow rate=80 ml / min; Gradient: 0-15% mobile phase B over 40 minutes; Mobile phase A=0.1% trifluoroacetic acid in water and Mobile phase B=0.1% trifluoroacetic acid in 90% acetonitrile). This yielded 510 mg of 2-amino adenosine as the pure product.
2-Fluoroadenosine
[0125] To a stirred solution of 0.15 g (0.53 mmo...
example 3
[18F]-2-Fluoroadenosine
[0126] A solution of [18F]-tetrabutylammonium fluoride in tetrahydrofuran (1-100 mCi) is added to 20 mg of 2-N,N,N-(trimethylammonium)adenosine triflate. This sample is incubated at 50° C. for 20 minutes after which the solvent evaporates. To obtain the title compound, the residue is purified by preparative reverse phase chromatography using the following method: 0-15% Mobile phase B over 40 minutes. Mobile phase A: 0.1% TFA in water; Mobile phase B: 0.1% TFA in 90% acetonitrile
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